Caroline County Public Schools Homes for Sale

Caroline County Public Schools Homes for Sale

**Discover Caroline County: A Great Place to Call Home**

Nestled in the heart of Virginia, Caroline County boasts a rich history and a vibrant community, making it an ideal place for families and individuals alike. One of the standout features of this charming county is the esteemed Caroline County Public Schools (CCPS), which is dedicated to providing a high-quality education and fostering a nurturing environment for students. With a range of educational programs and extracurricular activities, CCPS prioritizes the academic and personal growth of each student, ensuring they are well-prepared for future success.

The school district is known for its commitment to excellence, featuring dedicated teachers and staff who go above and beyond to inspire students. With a focus on innovation and technology, CCPS integrates modern teaching methods that engage students and encourage critical thinking. Parents can rest easy knowing their children are receiving a top-notch education in a supportive community.

As you explore the homes for sale in Caroline County, you'll find a diverse selection of properties that cater to various lifestyles and budgets. From charming single-family homes to spacious estates, there’s something for everyone. The real estate market here is thriving, offering new residents the chance to settle in a friendly neighborhood with access to excellent schools, parks, and local amenities.

Whether you’re drawn to the scenic landscapes, the welcoming community, or the outstanding educational opportunities, Caroline County is a place where you can create lasting memories. Come discover your dream home in this beautiful county, where quality living meets exceptional schooling!

Newest Caroline County Public Schools Homes for Sale

$99,000
3 Beds ⋅ 2 Baths
AS IS! GREAT INVESTMENT PROPERTY! This charming 3-bedroom, 1-bathroom traditional home, built in 1944, offers a solid investment opportunity with its AS IS condition gives you a blank slate to modernize this home to fit your needs! The traditional floor plan maximizes space, creating a warm and inviting atmosphere perfect for comfortable living. With a manageable lot size of 0.09 acres, maintenance is simplified, allowing for a focus on maximizing rental income or future resale value. The property features off-street parking, enhancing convenience for tenants or guests. Investors will appreciate the potential for appreciation in this desirable area, coupled with the opportunity to enhance the property further through updates or renovations. This home is not just a residence; it's a canvas for future growth and profitability. Don't miss the chance to add this gem with all its potential to your portfolio!

101 S University Ave, Federalsburg

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$955,000
3 Beds ⋅ 3 Baths
Private Waterfront Retreat on the Choptank River Experience the best of Eastern Shore waterfront living in this exceptional home built in 2021, where modern luxury, privacy, and serene views come together on one remarkable property. Situated on 8.15± private acres with approximately 600 feet of Choptank River frontage and deep water access, this stunning retreat offers the perfect balance of refined living and peaceful seclusion. Featuring 2,376± square feet of beautifully designed living space with modern finishes throughout, this home was thoughtfully crafted for effortless entertaining and everyday comfort. The open concept design seamlessly connects the kitchen, dining, and living areas, including a spacious sunroom with expansive windows for a bird's eye view of the river frontage. The main floor also includes an easily accessible large primary suite. Two additional bedrooms, full bath, and a dedicated pocket office or potential walk in closet can be found on the second level. Over the large garage, a full staircase provides access to a spacious bonus room, providing storage space currently, though could potentially serve as flexible space for guests, a media room, home gym, or playroom, per county approval. Step outside to discover a true waterfront oasis. Fresh landscaping complements the natural beauty of the property, while three acres of manicured lawn blend seamlessly into five acres of mature woods, creating ideal privacy and a picturesque setting. Whether hosting gatherings with family or friends, enjoying dinner or cocktails on the patio or dock, or relaxing with your morning coffee overlooking the peaceful scenery, every moment is enhanced by the tranquil surroundings. A new private pier with approximately 12 feet of water depth offers outstanding access to the Choptank River, making it easy to spend your days boating, fishing, kayaking, paddleboarding, or simply taking in spectacular sun painted skies from your own backyard. Ideally located near the town of Denton with lovely shops and restaurants, the location of this sanctuary is just a short drive to the Eastern Shore's most desirable destinations where there is convenient access to the boutique shopping, award winning restaurants, galleries, and downtown charm of Easton, the historic waterfront town of St. Michaels, and even excellent ocean beaches only one hour away. This property provides the perfect blend of privacy while keeping you close to everything that makes Maryland's Eastern Shore so special. More than just a home, this is a lifestyle where every day feels like a getaway and every season brings new opportunities to relax, entertain, and enjoy the beauty of private waterfront living.

8851 New Bridge Rd, Denton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$170,000
2 Beds ⋅ 1 Baths
Escape the noise and reconnect with what matters most. Nestled on a peaceful 1-acre country setting surrounded by mature trees and open skies, this charming cottage offers the perfect opportunity to embrace the simplicity and serenity of tiny home living. Whether you’re searching for a full-time residence, a weekend retreat, or a place to slow down and enjoy nature, this property delivers a lifestyle that’s becoming increasingly hard to find. Thoughtfully cared for and recently improved, the home features updated insulation, an upgraded electrical box, several newer windows, and the added comfort of a wall-mounted propane heater, providing a secondary heat source for cozy winter days. Outside, you’ll find endless possibilities with three detached outbuildings. Two are ideal workshop spaces for woodworking, hobbies, crafting, or storing equipment, while the detached one-car garage provides additional parking and storage. The expansive yard offers room for gardening, outdoor entertaining, or simply enjoying the sights and sounds of the surrounding countryside. Located just a short drive from historic downtown Denton, you’ll enjoy local restaurants, shops, community events, parks, the Choptank River, Martinak State Park, kayaking, fishing, hiking, and easy access to Maryland’s Eastern Shore attractions while still coming home to the peace and privacy of rural living. If you’ve been dreaming of a slower pace, simpler living, and a place where nature becomes part of your everyday routine, this inviting country cottage is ready to welcome you home. Conventional or cash sale only due to ceiling height.

6140 Laurel Grove Rd, Denton

Listing courtesy of Compass. Contact: 3022029855
$769,000
3 Beds ⋅ 3 Baths
Beautiful landscaped WATERFRONT

520 Lake Caroline Dr, Ruther Glen

Listing courtesy of Samson Properties. Contact: (703) 378-8810
$429,499
6 Beds ⋅ 3 Baths
LOVELY Tidewater Farms home with a light, open layout and plenty of space to enjoy. The main level features a spacious breakfast room, open kitchen and great room with a center island, eat-at bar, and gas fireplace. There is also a 19' x 15' bonus room and convenient upstairs laundry. The primary suite offers walk-in closets, a soaking tub, separate shower, and double sink vanity. Outside, enjoy the patio, storage shed, and white panel fence. The home has a brand-new roof from last year, HVAC upgraded approximately five years ago, brand-new washer and dryer, good plumbing, and a finished crawl space. Appliances are under warranty. The sellers are in the process of transitioning into their new home, so buyers should plan for a few months before possession. Reach out for additional information and pictures of the property!

304 Tidewater Cir, Preston

Listing courtesy of Samson Properties. Contact: 3018500255
$629,900
4 Beds ⋅ 3 Baths
Private waterfront retreat less than 90 minutes from Washington DC & Richmond in amenity rich Lake Caroline. Fully renovated home with private lakefront living on one of the community’s most desirable DOUBLE Lots (nearly one acre w/space for parking, RV, detached garage etc.) This beautifully remodeled home offers over 120 feet of private water frontage w/your own dock, creating a perfect backdrop for boating, fishing, or soaking in peaceful views. This home features a new roof, new HVAC, and luxury vinyl plank flooring throughout. Stunning chef’s kitchen, complete with custom cabinetry, under-cabinet lighting, quartz countertops, a spacious island, wine cooler, and a premium KitchenAid gas cooktop with electric oven—designed to impress and built for entertaining. The open dining area captures picturesque lake views, while the all-brick gas fireplace adds warmth to the living space. Redesigned mudroom/laundry area offers custom built-ins for added convenience, along with a large half bath and a versatile 4th bedroom—perfect for guests, a home office, or flex space. The primary suite is features a beautifully updated bathroom w/modern finishes and a tiled walk-in shower. Upgraded fully encapsulated crawl space w/dehumidifier & alarm making a moisture free added storage area. Enjoy lake life w/gatherings on the expansive back deck, relax in the fenced backyard, or explore your green thumb with the custom-built 12x12 greenhouse, mature landscaping, fruit trees, & thoughtfully designed garden beds leading down to the water. Freshly painted storage shed. This expansive lot has incredible potential—add a detached garage, or create your dream outdoor oasis. All of this is located within the amenity-rich Lake Caroline community, offering a pool, clubhouse, tennis and basketball courts, security, and more. This is more than a home—it’s a Lake lifestyle. Enjoy boating, fishing, paddleboarding, gas powered boats and jet skis permitted. INCLUDES FREE HOME WARRANTY & 1 YEAR HOA PREPAID DUES! Don't miss this rare opportunity!

448 Lake Caroline Dr, Ruther Glen

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$435,000
3 Beds ⋅ 2 Baths
Possibilities! This Caroline County 3-bedroom 2 bath Victorian sitting on almost 4 acres with fencing and plenty of usable buildings in a country setting. Nearby points of interest include Tuckahoe state park with equestrian trails, hiking trails, even a lake to paddle or fish. Gooden Airpark is just down the road along with a few boat ramps to the Choptank River. The property offers several mechanical upgrades including a recent new boiler for the hot water and heating system, recent BATT septic system installation, recent cooling system upgrades, a car charging hookup with upgraded service. The property is offered in as-is condition. Let's set up an appointment to take a look

13166 Oakland Rd, Ridgely

Listing courtesy of The Land Group. Contact: (410) 934-3478
$109,000
3 Beds ⋅ 1 Baths
Discover the potential in this ranch-style home situated on a spacious lot in Caroline County. This property is ready for renovation and offers a great opportunity to update and customize to your vision. Major improvements have already been completed, including a newer roof and updated windows, providing a solid starting point for your renovation plans. The home is served by a private well and septic system and offers the charm of country living with convenient access to Preston and surrounding areas. Bring your ideas and restore this property to its full potential.

4471 Harmony Rd, Preston

Listing courtesy of XRealty.NET LLC. Contact:

$225,000
4 Beds ⋅ 2 Baths
Opportunity awaits on this peaceful 1.46± acre wooded parcel in Preston. Tucked among mature trees, this property offers a private country setting with endless potential for its next chapter. The existing ranch-style home is being conveyed as part of an estate and is being sold AS-IS, including all remaining personal property and contents. Buyers should plan to complete their own due diligence regarding the condition of the home. Whether you're searching for your next renovation project or envisioning the possibilities this beautiful homesite has to offer, this property provides a rare chance to invest in a quiet, rural setting. No Inside Photos

21579 Tanyard Rd, Preston

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$575,000
4 Beds ⋅ 3 Baths
Photos Coming Soon. You'll love this custom home nestled on 2.13 private acres, offering nearly 2,500 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 baths. The open floor plan is highlighted by rich Brazilian hardwood floors, cathedral ceiling, and a welcoming great room anchored by a dramatic floor-to-ceiling brick fireplace. The spacious kitchen opens seamlessly to the great room and features an island, abundant cabinetry, generous counter space, and a built-in breakfast area. The formal dining room provides the perfect setting for holiday meals and special occasions. Relax in the spacious family room or the bright four-season room that overlooks the backyard. Designed for both entertaining and everyday enjoyment, the outdoor living space features a private in-ground pool. Whether taking a refreshing swim or relaxing on the screened porch while family and friends enjoy the pool, this backyard provides the perfect setting for summer gatherings or peaceful evenings at home. The oversized two-car garage offers exceptional space for hobbies, projects, or additional storage. This home combines quality craftsmanship, spacious living areas, and exceptional indoor and outdoor amenities, offering the perfect balance of privacy and comfort. 2 zones, 2 heat pumps, 3 and 8 yrs old. Solar is leased. Last years Solar lease bill plus electric bill averaged $228 a month. Roof is less then 5 years old

22733 Squire Ln, Queen Anne

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$259,900
2 Beds ⋅ 1 Baths
The joy of one level living!! This home is in Move-in ready condition. Nice size 2 Bedroom 1 Full Bath. Level lot with Patio for enetertaining. Conveniently located within town limits. Shop, parks, restuarants, Brewery. Public Boat ramp to the Choptank River less than a mile.

325 Carter Ave, Denton

Listing courtesy of Brenton Realty Group. Contact: 4104794663
$465,000
3 Beds ⋅ 2 Baths
Eastern Shore living at its finest! Nestled in the desirable Tuckahoe Springs subdivision, this beautifully maintained home offers the perfect blend of comfort, style, and serene outdoor living. Step inside to an inviting foyer that leads to a dedicated laundry area and an expansive, well‑appointed kitchen featuring cabinetry galore, upgraded stainless‑steel appliances, and quartz countertops. The kitchen flows seamlessly into a bright dining area accented with custom shiplap, creating an ideal space for everyday meals or entertaining. The formal living room is a true showstopper—anchored by a whitewashed brick wood fireplace and bathed in natural light, it’s the perfect place to unwind. Down the hall, you’ll find a guest bathroom, two comfortable bedrooms, and the private primary suite. The full basement expands your living possibilities with additional recreational space, thoughtfully divided into a potential living area and a generous storage section. Off the dining room, the spacious sunroom provides year‑round enjoyment, offering peaceful views of the backyard oasis. Outdoors, tranquility awaits. The backyard has been thoughtfully transformed with multiple gathering spaces including a cozy fire pit area, dedicated grilling zones, garden beds, and a private yard that captures the true Eastern Shore peace and quiet. The neighborhood also provides a private community water access to the Tuckahoe Creek with a picnic area and dock. This is your chance to experience a home that offers comfort, character, and the lifestyle you’ve been searching for. Don’t miss the opportunity to make this incredible property yours. Roof, HVAC, Septic and multiple other upgrades completed since 2022, providing the peace of mind you want in your next home!

23118 Tuckahoe Springs Dr, Denton

Listing courtesy of Brenton Realty Group. Contact: 4104794663
Start Your Search